Book Holiday Homes in Oswego

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Featured Holiday Homes in Oswego

Fox River Retreat

Fox River Retreat

St. Charles
Located in St. Charles, this vacation home is on a river, within a 10-minute drive of St. Charles Heritage Center and Camp Kane and Arcada Theater.
Fox River Retreat
Furnished Private home in Aurora

Furnished Private home in Aurora

Aurora
Located in Aurora, this vacation home is within a 5-minute drive of Copley Memorial Hospital and Rush-Copley Medical Center.
Furnished Private home in Aurora
King Bed, DIsney+, Spacious, Family-Friendly House

King Bed, DIsney+, Spacious, Family-Friendly House

Joliet
The price is AU$583 per night from 2 Dec to 3 Dec
AU$583
includes taxes & fees
2 Dec - 3 Dec
With a stay at this vacation home in Joliet, you'll be within a 15-minute drive of Harrah's Casino and Route 66 Raceway.
King Bed, DIsney+, Spacious, Family-Friendly House
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Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve

Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve

2 out of 5
Willowbrook
Located in Willowbrook, this vacation home is a 3-minute drive from Willowbrook Community Park and 5 minutes from Creekside Park.
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Spacious Deck & Balcony, Game Area, Garage

Spacious Deck & Balcony, Game Area, Garage

Glen Ellyn
The price is AU$746 per night from 24 Nov to 25 Nov
AU$746
includes taxes & fees
24 Nov - 25 Nov
Located in Glen Ellyn, this vacation home is a 5-minute drive from College of Dupage and 6 minutes from French Market.
Spacious Deck & Balcony, Game Area, Garage
Clarendon Hills Top Floor

Clarendon Hills Top Floor

Clarendon Hills
With a stay at this vacation home in Clarendon Hills, you'll be within a 5-minute drive of Ty Warner Park and Twin Lakes Park.
Clarendon Hills Top Floor
Charming 3-bedroom house in fantastic Plainfield,  10 min to Naperville

Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville

2 out of 5
Plainfield
A stay at this vacation home places you in the heart of Plainfield, within a 5-minute drive of Electric Park and Settlers Park.
Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
The price is AU$447 per night from 2 Dec to 3 Dec
AU$447
includes taxes & fees
2 Dec - 3 Dec
With a stay at this vacation home in Wheaton, you'll be within a 5-minute drive of Wheaton College and Dupage County Historical Museum.
✽ Charming Cottage ✽ close to College/Town/Station
Spread out - Renovated 5BR+Loft, Sleeps 12+

Spread out - Renovated 5BR+Loft, Sleeps 12+

Aurora
With a stay at this vacation home in Aurora, you'll be within a 5-minute drive of Aurora Regional Fire Museum and Hollywood Casino Aurora.
Spread out - Renovated 5BR+Loft, Sleeps 12+
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oswego Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oswego vacation homes are the perfect way for you to wing it.

Holiday houses in Oswego let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oswego in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oswego adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oswego with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oswego vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oswego Holiday Homes essential information

Accommodation
147 Holiday Homes
Lowest Price
AU$100
Highest Price
AU$746
Popular accommodation
Fox River Retreat, Furnished Private home in Aurora, King Bed, DIsney+, Spacious, Family-Friendly House, Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve, Spacious Deck & Balcony, Game Area, Garage , Clarendon Hills Top Floor, Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville, ✽ Charming Cottage ✽ close to College/Town/Station, Spread out - Renovated 5BR+Loft, Sleeps 12+

Top trending hotels in Oswego

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr, Oswego, IL
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 23 Dec to 24 Dec
AU$182
includes taxes & fees
23 Dec - 24 Dec
Located in Oswego, Best Western Oswego Hotel is within a 5-minute drive of Parkside Lanes and Aurora Skate Center.
Best Western Oswego Hotel
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
The price is AU$100 per night from 23 Dec to 24 Dec
AU$100
includes taxes & fees
23 Dec - 24 Dec
When you stay at Red Roof Inn PLUS+ Chicago - Willowbrook in Willowbrook, you'll be in the suburbs, within a 5-minute drive of Willowbrook Community Park and ...
Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is AU$191 per night from 28 Nov to 29 Nov
AU$191
includes taxes & fees
28 Nov - 29 Nov
Located in Willowbrook, The Champagne Lodge & Luxury Suites is a 4-minute drive from Willowbrook Community Park and 6 minutes from Burr Ridge Village ...
The Champagne Lodge & Luxury Suites
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DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 28 Nov to 29 Nov
AU$135
includes taxes & fees
28 Nov - 29 Nov
Located in Naperville, DoubleTree by Hilton Lisle Naperville is in the business district, a 2-minute drive from Morton Arboretum and 6 minutes from College of ...
DoubleTree by Hilton Lisle Naperville
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See all available properties in Oswego
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.